Sodium Hydroxide → HCID 22998298, compound

Temperature

95 °C

3-Chloro-10,11-dihydro-5H-dibenz[b,f]azepine (3.82 g, 16.6 mmol) was dissolved in toluene (20 ml). A solution of 3-chloropropionylchloride (2.53 g, 19.9 mmol) in toluene was added dropwise, and the resulting mixture was heated to 95° C. and stirred at that temperature for 30 minutes. The mixture was stirred overnight at room temperature. Further 3-chloropropionylchloride (2.53 g, 19.9 mmol) was added and the mixture was stirred at 95° C. for 1.5 h. After cooling, 0.2 M sodium hydroxide (10 ml) was added, and the phases were separated. The organic phase was diluted with more toluene (50 ml); and washed with first 0.2 M sodium hydroxide (6×10 ml) and then with more 0.2 M sodium hydroxide (3×20 ml) until the aqueous phase was alkaline. The organic phase was washed with water (3×15 ml), brine (25 ml), and dried (MgSO4). Evaporation in vacuo afforded 5.23 g (98%) of crude 3-chloro-1-(3-chloro-10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanone as an oil. This was further purified by addition of a mixture of heptane and ethyl acetate (1:1). This afforded 3.14 g (59%) of the product as a solid.

1. stirringThe mixture was stirred overnight at room temperature
2. stirringthe mixture was stirred at 95° C. for 1.5 h
3. temperatureAfter cooling
4. customthe phases were separated
5. additionThe organic phase was diluted with more toluene (50 ml)
6. washand washed with first 0.2 M sodium hydroxide (6×10 ml)
7. washThe organic phase was washed with water (3×15 ml), brine (25 ml)
8. dry with materialdried (MgSO4)
9. customEvaporation in vacuo

ORD record

ord-75b329b0379a45448be7f8c0719643e1

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613791B1